O,O-diethyl 1,1-difluoro-2-[(4R,5S)-2-oxo-5-phenyl-1,3-oxazolidin-4-yl]ethylphosphonothioate | 1178980-53-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: O,O-diethyl 1,1-difluoro-2-[(4R,5S)-2-oxo-5-phenyl-1,3-oxazolidin-4-yl]ethylphosphonothioate
• 英文别名: (4R,5S)-4-(2-diethoxyphosphinothioyl-2,2-difluoroethyl)-5-phenyl-1,3-oxazolidin-2-one
• CAS: 1178980-53-4
• 化学式: C₁₅H₂₀F₂NO₄PS
• 分子量: 379.365
• InChiKey: AIAPLXUCHQAJSR-OLZOCXBDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  88.9
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  O,O-diethyl (3R,4S)-3-[(tert-butoxycarbonyl)amino]-1,1-difluoro-4-hydroxy-4-phenylbutylphosphonothioate 、 N,N'-羰基二咪唑 在 三氟乙酸 、 N-甲基吗啉 作用下， 以 二氯甲烷 、 四氢呋喃 为溶剂， 反应 14.0h， 以56%的产率得到O,O-diethyl 1,1-difluoro-2-[(4R,5S)-2-oxo-5-phenyl-1,3-oxazolidin-4-yl]ethylphosphonothioate
  参考文献：
  名称：

  Diastereoselective Synthesis of γ-Amino-δ-hydroxy-α,α-difluorophosphonates: A Vehicle for Structure−activity Relationship Studies on SMA-7, a Potent Sphingomyelinase Inhibitor

  摘要：

  A highly diastereoselective synthesis of 2-amino alcohol derivatives bearing a difluoromethylphosphonothioate group at the 3-position was achieved through LiAlH(O-t-Bu)(3)-mediated reduction of the corresponding alpha-amino ketones. The phosphonothioate moiety of the product was readily converted into the corresponding phosphonate by oxidation with m-CPBA, followed by aqueous workup. The developed methods should be useful for SAR studies of SMA-7, a potent inhibitor of SMases.

  DOI：

  10.1021/jo9008782

文献信息

• Diastereoselective Synthesis of γ-Amino-δ-hydroxy-α,α-difluorophosphonates: A Vehicle for Structure−activity Relationship Studies on SMA-7, a Potent Sphingomyelinase Inhibitor
  作者：Takehiro Yamagishi、Shin Muronoi、Sadao Hikishima、Hiroshi Shimeno、Shinji Soeda、Tsutomu Yokomatsu

  DOI：10.1021/jo9008782

  日期：2009.8.21

  A highly diastereoselective synthesis of 2-amino alcohol derivatives bearing a difluoromethylphosphonothioate group at the 3-position was achieved through LiAlH(O-t-Bu)(3)-mediated reduction of the corresponding alpha-amino ketones. The phosphonothioate moiety of the product was readily converted into the corresponding phosphonate by oxidation with m-CPBA, followed by aqueous workup. The developed methods should be useful for SAR studies of SMA-7, a potent inhibitor of SMases.